Dick Costolo brings an unusual background as a former improv comedian at Second City who became Twitter's CEO and scaled the company from $0 to over $2B in annual revenue, now applying improv principles like listen first and yes-and to coach portfolio CEOs on communication and culture building. At 01 Advisors, he focuses specifically on companies that have found product-market fit and need help scaling go-to-market and leadership in the late Series A to early Series B stage, drawing from his experience running a real-time, everyone-watching platform to help founders stay calm and make disciplined decisions under public scrutiny.

• High regard for design-centric, next-generation software products. Frequently praises companies like Linear, Figma, and Attio for having founding teams with a powerful design sensibility that results in elegant, simple tools. Specifically points to the artisan-like focus and careful thinking of founders who ensure no corner of the product is unworthy of attention.
• Admiration for founders who are independent thinkers and control their own storytelling. Highlights leaders who develop their own narratives and explore domains outside their immediate focus, such as the founders of Linear and Stripe. Notes that the "Stripe mafia" is emerging as a significant talent pool similar to the early PayPal team.
• Interest in longevity, health span, and physical mobility. Follows the work of Bryan Johnson regarding life extension and emphasizes the importance of maintaining mobility through specific exercises like coil squats and horse stance squats before joint issues arise.
• Enthusiasm for the culinary arts and the dedication required to master cooking. Shares experiences of spending weeks cooking in Italian kitchens to learn the craft, noting that cooking is a discipline where one cannot fake expertise and must respect the process.
• Focus on practical management advice and continuous learning. Recommends resources that offer tangible guidance for company building, such as Bill Gurley's book on career management and Claire Hughes Johnson's work on scaling organizations.
• Support for urban innovation and the revitalization of San Francisco. Defends autonomous vehicle technology like Waymo against hyperbolic safety criticisms and recognizes efforts to improve city governance and functionality.